A1 Refereed original research article in a scientific journal
KINETICS AND MECHANISM OF THE ACID-CATALYZED HYDROLYSIS OF REGIOISOMERIC BENZOTRIAZOLE AND 8-AZAADENINE NUCLEOSIDES
Authors: KAPPI R, KAZIMIERCZUK Z, JARVINEN P, SEELA F, LONNBERG H
Publisher: ROYAL SOC CHEMISTRY
Publication year: 1991
Journal:: Royal Society of Chemistry. Journal: Perkin Transactions 2
Journal name in source: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Journal acronym: J CHEM SOC PERK T 2
Issue: 5
First page : 595
Last page: 600
Number of pages: 6
ISSN: 0300-9580
DOI: https://doi.org/10.1039/p29910000595
Abstract
First-order rate constants for the acid-catalysed hydrolysis of ribo- and 2'-deoxyribonucleosides derived from 1H-, 2H- and 3H-benzotriazoles and 7H-, 8H- and 9H-8-azaadenines have been determined over a wide pH range. Partial rate constants for reactions via mono- and di-protonated substrates have been calculated with the aid of spectrophotometrically determined pK(a) values. The mechanisms of hydrolysis reactions have been elucidated by the effects that polar substituents on the base moiety exert on the protonation and heterolysis steps. Reactivities of various regioisomers have been compared, and reasons for the exceptional hydrolytic instability of N3-alkylated purine nucleosides briefly discussed.
First-order rate constants for the acid-catalysed hydrolysis of ribo- and 2'-deoxyribonucleosides derived from 1H-, 2H- and 3H-benzotriazoles and 7H-, 8H- and 9H-8-azaadenines have been determined over a wide pH range. Partial rate constants for reactions via mono- and di-protonated substrates have been calculated with the aid of spectrophotometrically determined pK(a) values. The mechanisms of hydrolysis reactions have been elucidated by the effects that polar substituents on the base moiety exert on the protonation and heterolysis steps. Reactivities of various regioisomers have been compared, and reasons for the exceptional hydrolytic instability of N3-alkylated purine nucleosides briefly discussed.
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